Abstract

In this work, the [2 + 2] cycloaddition of fullerenes with the carcinogen BaPe was examined using the DFT method, with the aim of inhibiting the carcinogenic process of the latter. The increase in the electrophilic character of the reagents by the functionalization with electron-withdrawing groups was shown. By the functionalization of C₆₀, an increase in the dipole moment and consequently in the solubility of these reagents was shown. Also, a significant improvement in this solubility for these reagents by the [2 + 2] cycloaddition with BaPe increasing the dipole moment was noted. The most favored electrophilic-nucleophilic interaction between C2 and C3 has been rationalized. In the gaseous phase, very asynchronous concerted mechanisms by functionalization were demonstrated for this type of fullerene cycloaddition. In addition, an insufficiency of the calculations for the prediction of the inhibition of the mutagenic process by forming the C₆₀CONH₂–2.5BaPe complex (the major product) was noted and therefore the inclusion of the effects of biological solvent (water) was mandatory. In the presence of water, a significant decrease in the activation barriers and reaction energies compared to those of the gaseous phase was shown, therefore, a kinetic and thermodynamic preference of the C₆₀CONH₂–2.5BaPe complex from this cycloaddition, is deduced.

中文翻译：

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富勒烯纳米结构衍生物的抗癌活性预测：DFT 计算

摘要

本工作利用DFT方法研究了富勒烯与致癌物BaPe的[2+2]环加成反应，旨在抑制后者的致癌过程。结果表明，通过吸电子基团的官能化，试剂的亲电特性有所增加。_{通过C 60}的官能化，显示出偶极矩的增加以及因此这些试剂的溶解度的增加。此外，还注意到通过与 BaPe 的 [2 + 2] 环加成增加了偶极矩，这些试剂的溶解度得到了显着改善。C2 和 C3 之间最受青睐的亲电-亲核相互作用已被合理化。在气相中，这种类型的富勒烯环加成通过官能化证明了非常异步的协同机制。此外，注意到通过形成 C ₆₀ CONH ₂ –2.5BaPe 络合物（主要产物）来预测诱变过程的抑制的计算不足，因此包含了生物溶剂（水）的影响。强制的。在水存在下，与气相相比，活化势垒和反应能显着降低，因此，推断出来自该环加成的 C ₆₀ CONH _{2 –2.5BaPe 络合物的动力学和热力学偏好。}